Gas separation membrane, gas separation module, gas separator, gas separation method, and polyimide compound

Abstract

A gas separation membrane includes a gas separation layer that contains the polyimide compound having the structural portion represented by Formula (1). A gas separation module includes the gas separation membrane, a gas separator includes the gas separation module, and a gas separation method is performed using the gas separation membrane. A 1 and A 2 represent a linking site, a hydrogen atom, a halogen atom, a carboxy group, a carbamoyl group, an acyl group, an acyloxy group, a sulfo group, a sulfamoyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyloxy group, an alkoxycarbonyl group, a non-fluorinated alkyl group, or an aryl group. Here, at least one of A 1 or A 2 represents a linking site.

What is claimed is: 
     
         1 . A gas separation membrane comprising:
 a gas separation layer which contains a polyimide compound having a structural portion represented by Formula (1),   
       
         
           
           
               
               
           
         
         in Formula (1), A 1  and A 2  represent a linking site, a hydrogen atom, a halogen atom, a carboxy group, a carbamoyl group, an acyl group, an acyloxy group, a sulfo group, a sulfamoyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyloxy group, an alkoxycarbonyl group, a non-fluorinated alkyl group, or an aryl group, provided that at least one of A 1  or A 2  represents a linking site. 
       
     
     
         2 . The gas separation membrane according to  claim 1 ,
 wherein the polyimide compound has a unit structure represented by Formula (2),   
       
         
           
           
               
               
           
         
         in Formula (2), R 2a  represents a tetravalent linking group, and R 2b  represents a divalent linking group, provided that at least one of R 2a  or R 2b  has the structural portion represented by Formula (1). 
       
     
     
         3 . The gas separation membrane according to  claim 2 ,
 wherein R 2a  in Formula (2) has the structural portion represented by Formula (1), and R 2a  is represented by any of Formulae (3-1) to (3-3),   
       
         
           
           
               
               
           
         
         in Formulae (3-1) to (3-3), Ar represents an aromatic ring, the symbol “*” represents a linking site, L 1 , L 2 , and L 3  represent a single bond or a divalent linking group, R 3a , R 3c , R 3d , R 3e , and R 3f  represent a substituent, R 3b  and R 3g  represent a hydrogen atom, a halogen atom, a carboxy group, a carbamoyl group, an acyl group, an acyloxy group, a sulfo group, a sulfamoyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyloxy group, an alkoxycarbonyl group, a non-fluorinated alkyl group, or an aryl group, and p1 to p5 represent an integer of 0 to 20. 
       
     
     
         4 . The gas separation membrane according to  claim 2 ,
 wherein R 2b  in Formula (2) has the structural portion represented by Formula (1), and R 2b  is represented by any of Formulae (4-1) to (4-3),   
       
         
           
           
               
               
           
         
         in Formulae (4-1) to (4-3), Ar represents an aromatic ring, the symbol “**” represents a linking site, L 4 , L 5 , and L 6  represent a single bond or a divalent linking group, R 4a , R 4c , R 4d , R 4e , and R 4f  represent a substituent, R 4b  and R 4g  represent a hydrogen atom, a halogen atom, a carboxy group, a carbamoyl group, an acyl group, an acyloxy group, a sulfo group, a sulfamoyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyloxy group, an alkoxycarbonyl group, a non-fluorinated alkyl group, or an aryl group, and p6 to p10 represent an integer of 0 to 20. 
       
     
     
         5 . The gas separation membrane according to  claim 3 ,
 wherein R 2b  in Formula (2) has the structural portion represented by Formula (1), and R 2b  is represented by any of Formulae (4-1) to (4-3),   
       
         
           
           
               
               
           
         
         in Formulae (4-1) to (4-3), Ar represents an aromatic ring, the symbol “**” represents a linking site, L 4 , L 5 , and L 6  represent a single bond or a divalent linking group, R 4a , R 4c , R 4d , R 4e , and R 4f  represent a substituent, R 4b  and R 4g  represent a hydrogen atom, a halogen atom, a carboxy group, a carbamoyl group, an acyl group, an acyloxy group, a sulfo group, a sulfamoyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyloxy group, an alkoxycarbonyl group, a non-fluorinated alkyl group, or an aryl group, and p6 to p10 represent an integer of 0 to 20. 
       
     
     
         6 . The gas separation membrane according to  claim 2 ,
 wherein R ea  in Formula (2) is represented by any of Formulae (I-1) to (I-28),   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         in Formulae (I-1) to (I-28), X 1  to X 3  represent a single bond or a divalent linking group, L represents —CH═CH— or —CH 2 —, R 1  and R 2  represent a hydrogen atom or a substituent that does not have a structural portion represented by Formula (1), and the symbol “*” represents a linking site. 
       
     
     
         7 . The gas separation membrane according to  claim 2 ,
 wherein R 2b  in Formula (2) is represented by Formula (II-a) or (II-b),   
       
         
           
           
               
               
           
         
         in Formula (II-a), R 3  represents a substituent which does not have the structural portion represented by Formula (1), and k1 represents an integer of 0 to 4, 
         in Formula (II-b), R 4  and R 5  represent a substituent which does not have the structural portion represented by Formula (1) or groups that are linked to each other to form a ring together with X 4 , ml and n1 represent an integer of 0 to 4, and X 4  represents a single bond or a divalent linking group, and 
         the symbol “**” represents a linking site. 
       
     
     
         8 . The gas separation membrane according to  claim 3   wherein R 2b  in Formula (2) is represented by Formula (II-a) or (II-b),   
       
         
           
           
               
               
           
         
         in Formula (II-a), R 3  represents a substituent which does not have the structural portion represented by Formula (1), and k1 represents an integer of 0 to 4, 
         in Formula (II-b), R 4  and R 5  represent a substituent which does not have the structural portion represented by Formula (1) or groups that are linked to each other to form a ring together with X 4 , ml and n1 represent an integer of 0 to 4, and X 4  represents a single bond or a divalent linking group, and 
         the symbol “**” represents a linking site. 
       
     
     
         9 . The gas separation membrane according to  claim 1 ,
 wherein the content of the structural portion represented by Formula (1) in the polyimide compound is 0.50 mmol/g or greater.   
     
     
         10 . The gas separation membrane according to  claim 1 ,
 wherein a toluene swelling ratio of the polyimide compound is 35% or less.   
     
     
         11 . The gas separation membrane according to  claim 1 ,
 wherein the gas separation membrane is a gas separation composite membrane which includes a gas permeating support layer and the gas separation layer.   
     
     
         12 . A gas separation module comprising:
 the gas separation membrane according to  claim 1 .   
     
     
         13 . A gas separator comprising:
 the gas separation module according to  claim 12 .   
     
     
         14 . A gas separation method which is performed using the gas separation membrane according to  claim 1 . 
     
     
         15 . A polyimide compound which is represented by any of Formulae (5) to (7), 
       
         
           
           
               
               
           
         
         in Formulae (5) to (7), Ar represents an aromatic ring, R 5a , R 6b , and R 7a  represent a tetravalent linking group, R 5b , R 6b , R 6c , R 7b , and R 7d  represent a substituent, R 5c  and R 7c  represent a hydrogen atom, a halogen atom, a carboxy group, a carbamoyl group, an acyl group, an acyloxy group, a sulfo group, a sulfamoyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyloxy group, an alkoxycarbonyl group, a non-fluorinated alkyl group, or an aryl group, L 7 , L 8 , and L 9  represent a single bond or a divalent linking group, and p11 to p15 represent an integer of 0 to 20. 
       
     
     
         16 . A polyimide compound which is represented by any of Formulae (8) to (10), 
       
         
           
           
               
               
           
         
         in Formulae (8) to (10), Ar represents an aromatic ring, R 8a , R 9a , R 9b , R 10a , and R 10c  represent a substituent, R 8b  and R 10b  represent a hydrogen atom, a halogen atom, a carboxy group, a carbamoyl group, an acyl group, an acyloxy group, a sulfo group, a sulfamoyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyloxy group, an alkoxycarbonyl group, a non-fluorinated alkyl group, or an aryl group, R 8c , R 9c , and R 10d  represent a divalent linking group, L 10 , L 11 , and L 12  represent a single bond or a divalent linking group, and p16 to p20 represent an integer of 0 to 20.